2-sulfanilamidopyrazine



" Patented May 20, 1 947 v Z-SULFANILAMIDOPYRAZINE Rudolph Conrad Ellingson, Evansville, 1111, art-- signer to Mead Johnson 85 Company, Evans 'ville,1nd., a corporation of Indiana No Drawing. Application February 5, 1941, Serial No. 377,523

' 2 Claims. (c1. zoo-239.6)

My invention relates to 2-sulfanilamidopyrazine, a pyrazine derivative related to the class of chemotherapeutic compounds used in the treatment of streptococcal and tions, of whichsulfanilamide, p-aminobenzenesulfonamide, is the prototype.

My compound is prepared by reacting Z-aminopyrazine with p-acetaminobenzenesulionyl chloride followed by deacetylation. The reactions involved may be represented as follows:

N HiN cmc oimosoioi Hv H l cmcoNOsom- 11 H cmooNOso, J HOH n FR 1 n H.N soiN J 01 1300011 I fonyl chlorides, e. g., p-propionylaminobenzenesulionyl chloride, might be used instead of the simpler p-acetylaminobenzenesu1ionyl chloride; the substitution of such obvious-chemical equivalents. would be thin the scope of my invention.

For the preparation of 2-(N -acetylsulfanilamide) pyrazine, I prefer the following procedure: Two and one-tenth parts by weight of Z-aminopyrazine are suspended in 6.4 parts of pyridine. To this suspension aminobenzenesulfonyl the reaction mixture preferably does not exceed 55 C. .The syrupy is warmed at about 50 C. for 2 hours. After cooling to room temperature, a cold solution of 1 part am aware that other p-acylaminobenzenesul- 5.5 parts of p-acetchloride are added, with, agitation, at such a rate that the temperature of pneumococcal infecweight of a solution containing 1 volume of condark brown reaction mixture crystallized from sodium hydroxide in 5.5 parts or water is added. The reaction mixture is warmed briefly at about C., then diluted with water. The brown solid which separates is collected and dried, and then purified by, crystallization from alcohol. The purified compound, 2-(N -acetylsulianilamido) pyrazine, forms colorless, needle-like crystals which melt with decomposition at from 250 to 252 C. This substance is soluble in acetone, alcohol, and acetic acid, and is only slightly soluble in water.

2-sulianilamidopyrazine may be obtained from V 2-(N -acetylsulfanilamido) pyrazine by hydrolysis with acidified alcohol. To accomplish this hydrolysis, I prefer the following procedure: ,One part by weight of 2-(N -acetylsulfanilamido) pyrazine is suspended in 15 parts by centrated hydrochloric acid and 4 volumes of 95% alcohol. The reaction mixture is refluxed for about 25 minutes, cooled and diluted with an equal volume of water. The resulting clear brown solution is neutralized with concentrated ammonium hydroxide, whereupon a solid separates. This solid is collected and dried, and then a acetic acid solution. This compound, 2-sulfanilamidopyrazine, forms colorless crystals which melt with decomposition at about 255 C., are soluble in acetic acid and ethanol and are slightly soluble in water.

I claim: 1

1. The sulfa pyrazine of the formula:

. H H NHQ-sor-Nn1 In prepared for use as a therapeutic.

2. A compound having the linkage:

N H H H H XQSOr-Ni In 1 N H Y in which X is 'a group hydrolyzable to --NI -Iz, and

inwhich Y is a cation prepared for use as a therapeutic.

RUDOLPH CONRAD meson. (References on following page) 3 4 wing eteren 1 record in th I ,23%; g, Reviews, vol. 27, No. 1, Au 1940, pp. 11 UNITED 5 Journal Amer. Chem. Soc., Ja 1940, pp. 160- Number Name t 161.

2,203,933 m June 4, 194 2oggurnal Amer. Chem. 500., Aug 1940,. 1999- FOREIGN mm Johmal Amer. Chem. 800., Aug" 1939, pp. 2032- Number Country Date 10 3, 1101.51.

512,145 Great Britain A 30, 1939 517,272 Great Britain Jan. 25,- 1940 

